Triethylamine → HCID 10152224, compound

HRID 1297795Notes

Reaction equation

HRID 1297795 reaction equation
C([Si](C)(C)[O:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([C:14]2([C:24]3[CH:29]=[C:28]([CH3:30])[C:27]([O:31][Si](C(C)(C)C)(C)C)=[C:26]([CH3:39])[CH:25]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][C:15]2=[O:23])=[CH:9][C:8]=1[CH3:40])(C)(C)C.[CH:43]([C:46]1[CH:47]=[C:48](B(O)O)[CH:49]=[CH:50][CH:51]=1)([CH3:45])[CH3:44].C(N(CC)CC)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl-].[NH4+]>C1COCC1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.O.ClCCl>[OH:31][C:27]1[C:26]([CH3:39])=[CH:25][C:24]([C:14]2([C:10]3[CH:9]=[C:8]([CH3:40])[C:7]([OH:6])=[C:12]([CH3:13])[CH:11]=3)[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:50]3[CH:49]=[CH:48][CH:47]=[C:46]([CH:43]([CH3:45])[CH3:44])[CH:51]=3)[C:15]2=[O:23])=[CH:29][C:28]=1[CH3:30]

Participants

11

Reactant 5

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 27734783-Isopropylbenzeneboronic acidHCID 58914719HCID 58914719, compound

Product 1

HCID 10152224HCID 10152224, compoundYield 31.2%

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Combine 3,3-Bis-[4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-phenyl]-1,3-dihydro-indol-2-one (0.350 g, 0.581 mmol), 3isopropylphenylboronic acid (0.190 g, 1.16 mmol), copper (II) acetate (0.106 g, 0.581 mmol), triethylamine (0.16 mL, 1.16 mmol), 4 angstrom molecular sieves, and dichloromethane (10 mL). Stir at room temperature overnight under ambient atmosphere. Filter the reaction through Celite. Elute through a column of silica gel with 70% dichloromethane in hexanes and concentrate. Dissolve the resulting compound (0.189 g, 0.268 mmol), in THF (4 mL). Add a solution of tetrabutylammonium fluoride (1.0 M) in THF (0.67 mL). Stir for 1 h. Add saturated aqueous ammonium chloride(10 mL), water and ethyl acetate (50 mL). Separate the layers and concentrate the organic layer in vacuo. Chromatograph on silica gel eluting with 25% to 50% ethyl acetate in hexanes to give 0.089 g (31%) of the title compound: mass Spectrum (ion spray): m/z=492(M+1); 1H NMR(DMSO-d6); δ8.36 (s, 2H), 7.54 (t, 1H), 7.41-7.37 (m, 2H), 7.32-7.27 (m, 3H), 7.16 (t, 1H), 6.83-6.80 (m, 5H), 3.05-3.01 (m, 1H), 2.13 (s, 12H), 1.28 (d, 6H).

Workup

  1. filtrationFilter
  2. customthe reaction through Celite
  3. washElute through a column of silica gel with 70% dichloromethane in hexanes
  4. concentrationconcentrate
  5. stirringStir for 1 h
  6. customSeparate the layers
  7. concentrationconcentrate the organic layer in vacuo

Sources & evidence

ORD record
ord-3eb42d3cc1964960a6ccc180f3ecc057
Source dataset
uspto-grants-2007_07
Patent number
US07250442B2

Reaction notes

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